This PowerPoint Presentation is all about AMINES. Their Properties , Isomerism , Basicities , IUPAC naming for amines and etc

1. AMINES
DAVE PONTOD
DEJIEH ENGASTON
JEFFERSON SALVA

2. Amines
•are organic compounds which
contain and are often actually
based on one or more atoms
of nitrogen.

3. BONDING CHARACTERISTICS OF NITROGEN
ATOMS IN ORGANIC COMPOUNDS
C N O
4 valence electrons 5 valence electrons 6 valence electrons
4 covalent bonds 3 covalent bonds 2 covalent bonds
no nonbonding 1 nonbonding 2 nonbonding
electron pairs electron pair electron pairs

4. STRUCTURE
AND
CLASSIFICATION
OF AMINES

5. •Amine is an organic derivative
of ammonia (NH3) in which
one or more alkyl, cycloalkyl,
or aryl groups are attached to
the nitrogen atom.

6. Amines are classified as :
a.primary(1°),
b.secondary(2°),
c.tertiary(3°)

7. • Primary Amines
-is an amine in which the
nitrogen atom is bonded to
one hydrocarbon group
and two hydrogen atoms.

8. • Secondary Amine
-is an amine in which the
nitrogen atom is bonded to
two carbon groups and
one hydrogen atoms.

9. Tertiary amine
-in which the nitrogen
atom is bonded to three
hydrocarbon groups and no
hydrogen atoms.

10. The functional group present
in a
a. Primary amine, -NH2 group.
b. Secondary and tertiary
amines possess substituted
amino groups.

11. IUPAC RULES FOR
NAMING
PRIMARY AMINES

12. •Rule 1: Select as the
parent carbon chain the
longest chain to which the
nitrogen atom is attached.

13. •Rule 2: Name the parent
chain by changing the –e
ending of the
corresponding alkane
name to -amine.

14. •Rule 3: Number the
parent chain from
the end nearest the
nitrogen atom.

15. •Rule 4: The position of
attachment of the nitrogen
atom is indicated by a
number in front of the
parent chain name.

16. •Rule 5: The identity and
location of any
substituents are appended
to the front of the parent
chain name.

17. •In diamines, the final –e of the
carbon chain name is retained for
ease of pronunciation.
•Thus the base name for a four
carbon chain bearing two amino
groups is butanediamine.

18. •Secondary and tertiary amines are
named as N-substituted primary
amines.
•The largest group bonded to the
nitrogen is used as the parent
amine name.

19. The names of the other groups
attached to the nitrogen are
appended to the front of the base
name, and N- or N,N- prefixes are
used to indicate that these groups are
attached to the nitrogen atom rather
than to the base carbon chain.

20. •The simplest aromatic amine,
a benzene ring bearing an
amino group, is called aniline.
•Other simple aromatic amines
are named as derivative of
aniline.

21. •In secondary and tertiary
aromatic amines, the
additional group/s attached
to the nitrogen atom are
located using a capital N-.

22. ISOMERISM
FOR
AMINES

23. •Constitutional isomerism in
amines can arise from several
causes.
•Different carbon atom
arrangements produce
isomers.

24. For secondary and tertiary
amines, different partitioning
of carbon atoms among the
carbon chains present
produces constitutional
isomers.

25. There are three C4 secondary;
carbon atom partitioning can be
two ethyl groups, a.propyl
group, and a methyl group, or
an isopropyl group and a methyl
group.

26. PHYSICAL
PROPERTIES
OF AMINES

27. •The methylamines (mono-, di-
, and tri-) and ethylamine are
-gases at room temperature and
-have ammonia-like odors.

28. •Most other amines are liquids,
and many have odors
resembling that of raw fish.
• A few amines, particularly
diamines, have strong,
disagreeable odors.

29. • The foul odor arising from dead fish
and decaying flesh is due to amines
released by the bacterial
decomposition of protein.
• Two of these “odoriferous”
compounds are the diamines
putrescine and cadaverine.

30. PUTRESCINE

31. CADAVERINE

32. •The boiling points of
amines are intermediate
between those alkanes
and alcohols of similar
molecular mass.

33. •Intermolecular hydrogen
bonding of amines involves
the hydrogen atoms and the
nitrogen atoms of the
amino groups.

34. •The boiling points of
amines are lower than
those of corresponding
alcohols

35. •The difference in
hydrogen-bond
strength results from
electronegativity
differences

36. •Amines with fewer than
six carbon atoms are
infinitely soluble in water.
•Even tertiary amines are
water-soluble

37. BASICITY OF
AMINES

38. •Amines, like ammonia, have a
pair of unshared electrons on
the nitrogen atom present.
•These unshared electrons can
accept a hydrogen ion of water.

39. •Thus both amines and
ammonia produce
basic aqueous
solutions.

40. IMPORTANT
GENERALIZATIONS
APPLY TO
SUBSTITUTED
AMMONIUM IONS

41. •1. Substituted ammonium ions are
charged species rather than neutral
molecules.
•2. The nitrogen atom in an
ammonium ion or a substituted
ammonium ion participates in four
bonds.

42. •In a neutral compound, nitrogen
atoms form only three bonds.
•Four bonds about a nitrogen atom are
possible, however, when the species
is a positive ion because the fourth
bond is a coordinate covalent bond.

43. RULES FOR
NAMING THE
POSITIVE IONS

44. •Rule 1. For alkylamines,
the ending of the name
of the amine is changed
from amine to
ammonium ion.

45. •Rule 2. For aromatic
amines, the final –e of
the name of the amine is
replaced by –ium ion.

46. AMINE
SALTS

47. •The reaction of an
acid with a base
(neutralization)
produce a salt.

48. •Because amines are
bases, their reaction
with an acid produces a
salt, an amine salt.

49. •An amine salt is an ionic
compound in which the positive
ion is a mono-, di-, or
trisubstituted ammonium ion
(RNH3 +, R3NH+) and the
negative ion comes from an acid.

50. •Amine salts can be obtained
in crystalline form (odorless,
white crystals) by
evaporating the water from
the acidic solutions in which
amine salts are prepared.

51. •An older naming system for
amine salts, still used in the
pharmaceutical industry, treats
amine salts as amine-acid
complexes rather than as ionic
compounds.

52. •In this system, the same
made from
dimethylamine and
hydrochloric acid is
named and represented as

53. •The cocaine molecule is
both an amine and an
ester; one amine and two
ester functional groups are
present.

54. •Cocaine hydrochloride,
-the amine salt, is a white
powder that is sorted and
injected intravenously. Free-
based cocaine is heated and its
vapors are inhaled.

55. •Cocaine users and dealers call
the water-insoluble form of the
drug
• “crack”
• “snow” and
•“coke”

56. •Many medication labels refer
to hydrochlorides or hydrogen
sulfates (from sulphuric acid),
indicating that the
medications are in a water-
soluble ionic (salt) form.

57. •Many higher-molecular-
mass amines are water-
insoluble; however,
virtually all amine salts
are water-soluble.

58. •Many people
unknowingly use acids to
form amine salts when
they put vinegar or lemon
juice on fish.

59. •Such actions convert
amines in fish (often
smelly compounds) to
salts, which are
odourless.

60. •The process of
forming amine salts
with acids is an easily
reversed process.

61. •Treating an amine salt
with a strong base such
as NaOH regenerates
the “parent” amine.

62. PROCESS OF
AMINE SALT
FORMATION

64. HETEROCYCLIC
AMINES

65. •A heterocyclic amine is
an organic compound in
which nitrogen atoms of
amine group aromatic or
nonaromatic ring system.

66. •Heterocyclic amines are the
most common type organic
compound gives structures
for a number of “key”
unsubstituted heterocyclic
amines.

67. •These compounds are the “parent”
compounds for numerous derivatives
that are important in medicinal,
agricultural, food, and industrial
chemistry, as well as in the
functioning of the human body.

68. •Heterocyclic amines are the
first heterocyclic compound
that we have encountered that
have nitrogen heteroatoms.

69. •In previous chapters, we have
discussed heterocyclic compounds
with oxygen as the heteroatom:
cyclic ethers; cyclic ketones; the
cyclic forms of hemiacetals and
acetals and cyclic esters.

70. THANK
YOU

72. PYRROLE

73. IMIDAZOLE

74. INDOLE